Propyl mercaptan → HCID 14348392, compound

HRID 1650736Notes

Reaction equation

HRID 1650736 reaction equation
BrBr.Cl[CH2:4][CH2:5][CH2:6][C:7](=[O:9])[CH3:8].[CH2:10]([SH:13])[CH2:11][CH3:12].[OH-].[K+]>C(Cl)Cl.CO>[C:7]([C:6]1([S:13][CH2:10][CH2:11][CH3:12])[CH2:4][CH2:5]1)(=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 7848Propyl mercaptanHCID 14797Potassium HydroxideHCID 24408BromineHCID 799932-Pentanone, 5-chloro-

Product 1

HCID 14348392HCID 14348392, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 134 g (0.83 mol) of bromine in 130 ml of methylene chloride is added dropwise at 10° C. with stirring to a solution of 100 g (0.83 mol) of 5-chloropentan-2-one in 400 ml of methylene chloride. The reaction mixture is stirred at room temperature for 1 hour, then washed with water and dilute, aqueous sodium carbonate solution and dried over sodium sulphate. The mixture is concentrated by removing the solvent under reduced pressure, and the residue is taken up in 200 ml of methanol and 63 g (0.83 mol) of n-propylmercaptan are added at 5° C. with stirring. A mixture of 93 g of potassium hydroxide powder in 500 ml of methanol are then added dropwise. The reaction mixture is first stirred at room temperature for 2 hours and then at 40° C. for 4 hours. The mixture is subsequently concentrated by removing the solvent under reduced pressure and the residue which remains is taken up in methylene chloride. The organic solution is washed successively with water, dilute aqueous sodium hydroxide solution and again with water, then concentrated under reduced pressure and then subjected to a vacuum distillation. In this manner, 42 g (32% of theory) of 1-acetyl-1-propylmercapto-cyclopropane of boiling point 107° C./20 mbar are obtained.

Workup

  1. washwashed with water
  2. additiondilute
  3. dry with materialaqueous sodium carbonate solution and dried over sodium sulphate
  4. concentrationThe mixture is concentrated
  5. customby removing the solvent under reduced pressure
  6. stirringwith stirring
  7. additionare then added dropwise
  8. stirringThe reaction mixture is first stirred at room temperature for 2 hours
  9. waitat 40° C. for 4 hours
  10. concentrationThe mixture is subsequently concentrated
  11. customby removing the solvent under reduced pressure
  12. washThe organic solution is washed successively with water, dilute aqueous sodium hydroxide solution and again with water
  13. concentrationconcentrated under reduced pressure
  14. distillationsubjected to a vacuum distillation

Sources & evidence

ORD record
ord-715344059119442590da94046fbbe590
Source dataset
uspto-grants-1990_05
Patent number
US04925865

Reaction notes

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